1,8-cineole synthase

1,8-Cineole synthase (EC 4.2.3.108, 1,8-cineole cyclase, geranyl pyrophoshate:1,8-cineole cyclase, 1,8-cineole synthetase) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming).[1][2][3][4][5] This enzyme catalyses the following chemical reaction

geranyl diphosphate + H2O 1,8-cineole + diphosphate
1,8-cineole synthase
Identifiers
EC no.4.2.3.108
CAS no.110637-19-9
Databases
IntEnzIntEnz view
BRENDABRENDA entry
ExPASyNiceZyme view
KEGGKEGG entry
MetaCycmetabolic pathway
PRIAMprofile
PDB structuresRCSB PDB PDBe PDBsum
Search
PMCarticles
PubMedarticles
NCBIproteins

This enzyme requires Mn2+ or Zn2+. Geranyl diphosphate first isomerizes to (S)-linalyl diphosphate which ionises to the alpha-terpinyl cation which reacts with water to form the product.[6]

References
  1. Croteau R, Alonso WR, Koepp AE, Johnson MA (February 1994). "Biosynthesis of monoterpenes: partial purification, characterization, and mechanism of action of 1,8-cineole synthase". Archives of Biochemistry and Biophysics. 309 (1): 184–192. doi:10.1006/abbi.1994.1101. PMID 8117108.
  2. Wise ML, Savage TJ, Katahira E, Croteau R (June 1998). "Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase". The Journal of Biological Chemistry. 273 (24): 14891–14899. doi:10.1074/jbc.273.24.14891. PMID 9614092.
  3. Peters RJ, Croteau RB (September 2003). "Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases". Archives of Biochemistry and Biophysics. 417 (2): 203–211. doi:10.1016/s0003-9861(03)00347-3. PMID 12941302.
  4. Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D (August 2004). "Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole". Plant Physiology. 135 (4): 1956–1966. doi:10.1104/pp.104.044388. PMC 520767. PMID 15299125.
  5. Keszei A, Brubaker CL, Carter R, Köllner T, Degenhardt J, Foley WJ (June 2010). "Functional and evolutionary relationships between terpene synthases from Australian Myrtaceae". Phytochemistry. 71 (8–9): 844–852. Bibcode:2010PChem..71..844K. doi:10.1016/j.phytochem.2010.03.013. PMID 20399476.
  6. Rinkel J, Rabe P, Zur Horst L, Dickschat JS (2016-11-04). "A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus". Beilstein Journal of Organic Chemistry. 12: 2317–2324. doi:10.3762/bjoc.12.225. PMC 5238540. PMID 28144299.
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